Water → Benzonitrile, 2-amino-6-(phenylthio)-

HRID 834

Reaction equation

HRID 834 reaction equation
O.[N+:2]([C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:6]=1[C:7]#[N:8])([O-])=O.Cl[Sn]Cl>COCCOCCOC.Cl>[NH2:2][C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:6]=1[C:7]#[N:8]

Participants

6

Reactant 3

HCID 962WaterHCID 24479Stannous ChlorideHCID 151982412-Nitro-6-(phenylthio)benzonitrile

Product 1

HCID 486276Benzonitrile, 2-amino-6-(phenylthio)-

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8150DiglymeSolvent

Procedure

To a water bath-cooled solution of 3.9 g (0.015 mol) of 2-nitro-6-(phenylthio)benzonitrile (Example 1) in 85 mL of diglyme was added dropwise, with stirring, 11.53 g (0.045 mol) of SnCl2.2H2 O in 35 mL of conc. HCl. The water bath was removed, and the reaction was stirred at room temperature for 0.5 h. This reaction mixture was poured into a vigorously stirring mixture of 100 mL of 50% NaOH and 300 g of crushed ice. Precipitate was collected by filtration and washed with 1N NaOH and water. Purification by flash column chromatography on silica gel with methylene chloride resulted in 2.3 g (68%) of 2-amino-6-(phenylthio)benzonitrile as a white solid: mp 73°-77° C.

Workup

  1. customThe water bath was removed
  2. stirringthe reaction was stirred at room temperature for 0.5 h
  3. additionThis reaction mixture was poured into
  4. stirringa vigorously stirring
  5. additionmixture of 100 mL of 50% NaOH and 300 g of crushed ice
  6. filtrationPrecipitate was collected by filtration
  7. washwashed with 1N NaOH and water
  8. customPurification by flash column chromatography on silica gel with methylene chloride
  9. customresulted in 2.3 g (68%) of 2-amino-6-(phenylthio)benzonitrile as a white solid

Sources & evidence

ORD record
ord-d850da0197e245649bff3ba3999f661f
Source dataset
uspto-grants-1998_03
Patent number
US05723452

Linked notes

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